5-Day Romantic Getaway in Chicago, USA

Discover the charm of Chicago's city lights and fall in love all over again.

22 April 2023

A romantic trip to Chicago, United States is the perfect opportunity to explore the Windy City together. You can take a stroll along the picturesque Lake Michigan shoreline, indulge in mouth-watering cuisine at award-winning restaurants, and take in the breathtaking views from the Willis Tower. With a wide range of cultural and entertainment options, Chicago provides the ideal backdrop for a memorable romantic getaway.

Travel plan

Getting latest place information
Day 1

Arriving in the Windy City

  • Check into the luxurious Waldorf Astoria for a romantic stay
  • Head to Millennium Park to see the iconic Cloud Gate sculpture
  • Enjoy a delicious dinner at the Michelin-starred Alinea restaurant
  • Take a stroll along the Chicago Riverwalk for stunning views of the city skyline
  • End the night with a cocktail at the swanky rooftop bar, Cindy's
Day 2

Art and Food

  • Start the day with breakfast at the trendy café, The Allis
  • Visit the Art Institute of Chicago, one of the best art museums in the world
  • Grab a bite to eat at the Chicago French Market, a bustling food hall of curated vendors
  • Take a scenic boat tour on the Chicago River to see the city's architecture
  • Have a romantic dinner at Boka, a chic restaurant serving contemporary American cuisine
Day 3

Exploring Chicago's Neighborhoods

  • Have a leisurely brunch at the charming Little Goat Diner in the West Loop
  • Take a walk through the vibrant Pilsen neighborhood to see colorful murals and graffiti art
  • Visit Wrigley Field, the iconic home of the Chicago Cubs
  • Experience the nightlife in Logan Square, home to trendy bars and restaurants
  • End the night with a nightcap at The Violet Hour, a stylish cocktail bar
Day 4

History and Shopping

  • Start the day with breakfast at Xoco, a Mexican-inspired café by celebrity chef Rick Bayless
  • Visit the Field Museum to learn about natural history and ancient civilizations
  • Take a stroll down the Magnificent Mile for premier shopping and retail therapy
  • Have a classic Chicago-style hot dog at Portillo's
  • Catch a theatre show at the legendary Chicago Theatre
Day 5

Farewell, Chicago

  • Enjoy a farewell breakfast at the quirky Batter & Berries in Lincoln Park
  • Visit the Navy Pier for carnival rides and stunning views of Lake Michigan
  • Take a final stroll around the picturesque Lincoln Park Zoo
  • End the trip with a romantic dinner at the upscale Harry Caray's Italian Steakhouse
  • Say goodbye to the Windy City with a nightcap at the speakeasy-style The Office.

How to get there

Plane

The best way to get to Chicago by plane is to fly into O'Hare International Airport or Midway International Airport, both of which are served by major airlines from most major cities in the world. You can check prices and schedules on websites like Expedia or Kayak.

Car

The best way to get to Chicago by car is to take one of the major highways, such as I-90 or I-94, which both run through the city. However, be aware of traffic congestion during peak travel times.

Train

The best way to get to Chicago by train is to take an Amtrak train, which connects the city to other major cities in the United States, such as New York, Washington D.C., and Los Angeles. The main train station in Chicago is Union Station.

Boat

The best way to get to Chicago by boat is to take a ferry from Navy Pier to locations such as Michigan City or St. Joseph. However, this mode of transportation is not as common as the others and may have limited availability depending on the season.

Bus

The best way to get to Chicago by bus is to take a Greyhound bus, which connects the city to most major cities in the United States. The main bus station in Chicago is the Greyhound Station.

More travel plans

The Ultimate 3-Day Chicago Adventure

Chicago boasts an impressive skyline and rich cultural diversity that attracts visitors from all over the world. Iconic landmarks such as the Willis Tower and Millennium Park provide excellent photo opportunities, while a stroll along the Magnificent Mile offers an extensive array of shopping, dining, and entertainment options. For a taste of Chicago's famous cuisine, deep-dish pizza and Chicago-style hot dogs are a must-try.

Chicago on a Budget: A Day of Adventure

Visiting Chicago on a limited budget is still possible with some careful planning. Opt for budget-friendly accommodation options such as hostels or Airbnbs in less touristy neighborhoods. Take advantage of public transportation and free activities such as visiting Millennium Park, the Lincoln Park Zoo, and exploring the city's diverse neighborhoods for a fun and affordable trip to Chicago.

Discover Chicago: A Family-Friendly Adventure on a Budget

A family-friendly trip to Chicago offers a perfect blend of fun and educational activities. Explore the interactive exhibits at the renowned Field Museum, embark on a scenic boat tour along the Chicago River, and get a stunning, panoramic view of the city from the Skydeck Chicago. Don't forget to indulge in some deep-dish pizza and visit the beloved Lincoln Park Zoo during your visit!

Chicago in 4 days: Romance, Art, and Adventure

A romantic trip to Chicago begins with a stroll along the picturesque Riverwalk, taking in the stunning views of the city’s skyline. Embark on a journey to the top of the Willis Tower to marvel at the spectacular panorama or catch a show at the iconic Chicago Theatre. Relax with a glass of wine or craft cocktail in one of the city’s rooftop bars, or indulge in a romantic dinner at one of its many acclaimed restaurants.